However, rolling out a new Operating System to (tens of) thousands of users is complex and requires a lot of upfront planning and preparation. In fact, based on our experience of readying more than 5 million assets for successful migration, we have concluded that almost 80% of an enterprise-size migration project is consumed by planning and readiness tasks, not in the technical task of migration itself. And since the the average project runs between 44 to 124 weeks, you have to have gone through some of the readiness steps already to position your organization to finish in 2017.

So, where are enterprise IT departments when it comes to Windows 10 readiness today? How prepared are they and what aspects are they particularly struggling with? We wondered the same thing. Over the past eight months, we asked 100 IT project managers, CIOs, and other IT professionals to assess their own Windows 10 readiness in an interactive quiz.

In particular, we wanted to know how they fare regarding:

Budget Allocation

Resource Planning

Desktop Management Infrastructure

Age Of The Current Hardware Estate

UEFI/TPM 2 Compliance Of Existing Hardware

Application Inventory Management

Application Testing Effort Required

Rationalization Of Applications

Packaging Strategy

Repository Of All In Scope Users, Locations, Computers, And Applications

Deployment Strategy

Today, we want to take a snapshot and take a closer look at where organizations are in their process.

More Than Half Of Organizations Have Budget Allocated

Allocating budget is a crucial first step in getting the ball rolling on your OS upgrade.

In a project of this size and complexity, there will be a significant requirement for resource budget, in addition to hardware budget for replacements and software budget for mandatory upgrades to fully take advantage of all that Windows 10 has to offer.

Most organizations understand that project funding is necessary. More than one-third of organizations (36%) have already fully, and 17% have at least partially allocated their budget.

On the other hand, 29% of project managers said they still need to create a business case and request funding, while a surprising 13% of IT professionals asked do not believe they need a budget to upgrade to Windows 10.

The remaining 6% have no firm timeline set for their migration.

(Not sure how much to allocate? Use the Budget Calculator to get a better idea what this project will cost you.)

Most Migrations Will Be Managed With Internal Resources

Whether you are planning to manage your Windows 10 rollout through a third-party service integrator, or by leveraging in-house resources, you need a waterproof resource management plan in place.

This plan should lay out exactly the skillset and capacity required to manage the migration of thousands of assets and users, as well as how you will handle associated tasks such as the rationalization of your hardware estate or the extensive application testing involved.

Most of the IT professionals we asked have already decided whether or not they will outsource, and the split is almost even:

44% are planning to migrate using internal resources, while

42% will outsource. Of those outsourcing, only

14% of companies have an outsourcing agreement in place,

While 28% are still planning to issue a request-for-proposal.

The remaining 14% have not decided yet how they will staff their migration project.

Outdated Desktop Management Tools Puts Organizations Behind

According to our research, two out of three organizations are using Microsoft SCCM 2012 (58%) or the latest version of an SCCM equivalent tool from another manufacturer (10%).

However, 12% of respondents indicated that they are using the older version of the SCCM 2007 (10%) or equivalent (2%) — which puts them behind the proverbial 8-ball as older versions of desktop management infrastructure will not support Windows Branching and without upgrade, will deliver suboptimal results.

Noteworthy here is also that one out of five (20%) IT departments currently do not have any desktop management tool in place today!

Aging Hardware Infrastructure

Intel's CEO announced mid-2016 that laptop refresh cycles can now be extended from 2-3 years to 5-6 years, which is great news, especially for larger organizations. However, to take advantage of that, you will have to upgrade to the newer versions of laptops and desktops first.

For Windows 10 Enterprise, the following system requirements must be met, although most organizations will procure a much higher level of hardware for performance:

Processor: 1 GHz or faster or SoC

RAM: 1 GB (32-bit) or 2 GB (64-bit)

Free hard disk space: 16 GB (32-bit) or 20 GB (64-bit)

Graphics Card: DirectX 9 or later with WDDM 1.0 driver

Display: 800x600

According to our research, more than half of organizations have a hardware estate in place that is between 2-4 years old (49%) or older than four years (12%), but the real number is likely to be a lot higher.

Of the IT professionals that responded, 25% have a mix of differently-aged hardware in place, which could indicate that they do not know exactly how old it is in reality. However, 3% of respondents admitted that they had no idea.

UEFI/TPM 2 Compliance

With aging hardware comes not only higher maintenance and support costs or loss of productivity, but you are also running the risk that you will not be able to take advantage of all the security features that Windows 10 has to offer because your hardware is not UEFI/TPM 2 compliant.

In fact, only 31% of organizations said that their entire hardware inventory is compliant, while 19% stated that most of the PCs and laptops met the requirements.

One out of four IT project managers said that some of their hardware was compliant, while 19% stated that they did not know.

Surprisingly, 5% of companies are not planning on taking advantage of any new security features.

Clean List Of Application Inventory

A clean inventory of all of your in-use applications will not only allow you to accelerate your migration significantly (as you will be able to rationalize your software estate), but it also enables you to save on software licenses and support costs down the road.

Of all IT professionals surveyed, one out of three responded that they have a clean list of applications and web applications, 30% have an up-to-date list of all applications, but not web applications.

And 9% of people asked stated that they only know which web applications they have.

On the opposite side of the spectrum, an astonishing 29% have no clue what their application landscape really looks like.

We asked IT project managers about how much testing they anticipate their in-house applications needed to gauge their readiness. Here are the results:

Only 16% of respondents said that all of their applications have already been tested.

While 25% had already tested some of their apps, 43% stated that most of their applications still needed testing.

16% were not sure.

So, in other words, most organizations are in the process or have not started tackling this step yet.

Application Rationalization & Packaging Strategy

Once you have a clean inventory of all of your applications and they have been tested for compatibility, it is time to rationalize your software estate. This way, you can cut down the number of versions you will have to bring over.

Regarding migration readiness, only 11% of organizations said they had already fully rationalized their application estate, and 26% had at least tackled some of their applications.

28% of respondents stated that they are monitoring application usage and retiring all unused applications, while 25% will ask their users and business contacts which applications they need.

The remaining 9% are planning on taking forward everything they have running out there today.

Based on that, it is not surprising that more than one out of three (36%) have not decided on how they will be delivering their applications for Windows 10. Another 36% already have a packaging strategy in place while the remaining 28% have a strategy, but are still in the process of writing standards for it.

47% Will Use A Central Project Management Tool

Traditionally, IT project managers struggled to keep a tab on their enterprise-size migration projects because they used instantly out-of-date spreadsheets and hand-cranked databases. But it does not have to be that way.

However, how are today's IT project managers planning on managing their Windows 10 rollout from a tooling perspective?

As part of our research, we asked: "Do you have a repository of all in scope users, locations, computers, and applications to provide central control & command?" and 47% said that they are planning to use anIT Migration Project Management Tool (data warehouse).

Surprisingly, more than half of the people will not: 28% of the IT professionals will continue to use spreadsheets because that is what they always did, and 25% will stitch together a database in-house that all feeds will go into.

Most Organizations Do Not Have A Detailed Deployment Strategy Yet

Finally — your deployment strategy. Once all the other planning is done, it is time to decide on a logical and comprehensive plan that outlines how you will handle the actual deployment.

Of course, this will need to take into account any time-critical procedures, like month-end reporting as that would be most disruptive to your everyday business operations, as well as any training and admin processes to minimize downtime.

While only 15% of enterprises have a detailed deployment scheduling and logistics strategy in place, 43% are on the track to outlining one. The remaining 42% do not have an implementation plan yet.

Conclusion

Based on the data above we can conclude that enterprises and other large organizations have mostly taken care of the easier parts of the migration process: most have allocated a full or partial budget, decided whether or not to use internal or external resources, already or almost a packaging strategy in place and have decided on tooling. Most IT professionals also know that their hardware estate is between 1-2 or 2-4 years old and that it is mostly compliant with Windows 10 security requirement.

It is encouraging to see that almost two thirds of companies are using the latest version of the SCCM (or equivalent) and that practically half of all IT project manager are planning to use a more sophisticated project management tool that spreadsheets or handcranked databases.

However, there are three gaping holes as well: Firstly, very few organizations have finished testing for application compatibility - the biggest roadbock to a smooth Windows 10 rollout. Secondly, only one out of 10 IT departments has completed the rationalization step and many are planning to either ask their users, retire as needed based on application usage or move everything forward. Lastly, organizations are struggling to put an efficient deployment strategy in place.

Barry is a co-founder of Juriba, where he is focused on using his experience in IT migration to help drive product strategy, pre-sales and service delivery. He is an experienced End User Services executive that has helped manage thousands of users, computers, applications and mailboxes to their next IT platform. He has saved millions of dollars for internal departments and customers alike through product, project, process and service delivery efficiency.